Unlock your creative energy ft. True Ventures’ partner, Kevin Rose

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If you missed last week’s newsletter and the tips on how to leverage your skillset for success ft. Senior Vice President of Marketing @Yelp, Dan Kimball you can find it here.

This week’s will be about True Ventures’ partner, Kevin Rose.

Kevin Rose is a partner at True Ventures, a VC firm that invests in early-stage tech startups. He focuses on blockchain, consumer internet, and health/wellness. Prior to his career at True Ventures, he was a GP at Google Ventures and a serial entrepreneur. He founded Digg, Zero, Oak, and other tech companies. He also invested in Twitter, Facebook, Square, Solana, Ripple, Nextdoor, Medium, Blue Bottle Coffee, and many other iconic companies.

Parts of this newsletter are freely taken from our interview and adjusted for reading. Everything a person says in the interview reflects the guest's and host’s opinion, not the newsletter's or brand's.

GG: You've started so many companies and experienced the ups and downs. What motivates you to do all these things? What have you experienced and learned throughout it?

KR: Creativity motivates me. I want to tinker and build new stuff and think of things that nobody's done before and try them out. The majority of what falls under that umbrella has failed, and that's okay. The number of times we fail is staggering. Many times, we don't realize that we're failing when we're building products. We try some features out, and they may not work, but that's not a failure. In reality, we're failing every single day. Once I became comfortable with that, it was a huge unlock for me. When Digg failed, I was depressed, there were a lot of things I messed up on. The big unlock for me at that moment was to stop hiding the things that I don't know and come out and raise my hand and say "I don't know this. Can you help me?" That was something I had a really hard time with. I didn't want to look foolish in front of my peers or people that I respected. The motivation side of it has never been something where I had to wake myself up and splash water in my face and say, "You've got to do this." It's never been that. It's always been just this natural, internal drive of wanting to create and wanting to build.

GG: Who is on your personal board of advisors for your career?

KR: I would say that I have a handful of close personal friends I look to for advice. They may not be the household names that you would expect. Tim Ferriss is on that list, and it's mostly people with whom I can have casual conversations without any pretense or walls. When I have a problem, I can call them and tell them what's going on. I believe having a relationship with someone is more important than just having their contact information. Even if you have the contact information of a Fortune 100 CEO, if you don't have a relationship with them, you won't get the help you need. So, I rely on former colleagues I've worked with and good personal friends that have known me for many years. They know the whole of me, and that's important because they can give me advice based on who I am. They can tell me if I should focus on something else instead of building another app or call me out when I'm not doing my best. They know you intimately enough to know your weaknesses and your strengths. I have around 10 people I can call up and discuss how things are going in my life, and I value their opinions. These are people that would do the same with me. We support each other. It's important to find friends like that rather than just choosing people who might look good on a press release. Of course, if you have tactical questions about scaling a business, it's great to have people to ask. However, for most things, it's more emotional and EQ-driven than IQ-driven.

GG: How do you identify what your strengths are and then how do you fix your weaknesses?

KR: I think that just being honest with yourself about admitting when you don't know something and then going to get schooled up in it it's important. Also, ask yourself "Do I enjoy doing it"? For example, I had never managed anyone before, never fired anyone, and I didn't know what a proper interview process looked like. Once I eventually raised my hand and went to people I respected to learn these skills, it was something that I enjoyed doing, until a point". When Zero was growing and it got off the ground, it got to a certain point where I said, "I don't want to do this anymore." I had worked with a fantastic product person, who worked with me at Digg and ran all of our marketing and PR and he said, "I can take this and scale it to the next level." So, I'm great at that with up to 10 to 15 people, then things slow down, and I'm a fast-paced, rapid-iteration type of person. Once I identified that, it was easy because I could bring someone in to run the business and then take it to where it is today. I realized that at Hodinkee as well. I was CEO there for a couple of years and when I was there, there were four or five of us in total. Now there are over 100 people at Hodinkee. I realized I could just get it to around 25 people or so and around $8 million a year in revenue, and I was like, "This is not what I enjoy doing. It's more management, less product." So, we brought in another CEO, and that business will do over $100 million in revenue this year, which is crazy. That's where I tap out, and so I'm good at the early creative iteration ideation phase. Being true to yourself, saying, "These are my strengths. This is what I enjoy," is the first step.

GG: Was there something that happened in your childhood that influenced you?

KR: I grew up in a household of builders, and we were standard middle-class. My dad declared bankruptcy when I was 15. However, my parents were both entrepreneurs, something I always respected. My dad had a bookkeeping business where he kept books for other local businesses and sold life insurance before that. He was always in business for himself, except for one time when he worked for a larger company. They were always thinking about how to have little side hustles, back in the early '90s - late '80s. My mom did nails, flower arrangements, and gift baskets, and she ran her business out of our home. I'd walk into the house during the holidays and see gift baskets everywhere, and she'd be wrapping up packages and building these things. It was then that I realized a job is just something you decide to build, and you form a business around it. When I was 16, my dad took me down to the business bureau in Las Vegas, and we filed an LLC called United Web. It was my first business, and he made me fill out the paperwork, including putting my name in there. He had to sign it since I was not yet 18 years old. He helped me open a checking account and took me to the bank and guided me in how things work. I never graduated from college and worked for other people in the Bay Area before starting my own thing. I knew software development was something I was really into, and it was just built in at that early stage that my parents would have always been proud if I started a business.

THIS WEEK’S QUOTE

GRACE WEEKLY - THE BEST INFORMATION DIET FOR FUTURE CEOs

What's the key takeaway from this? Thinking outside the box and coming up with unique solutions is fundamental for staying ahead of the curve. An entrepreneur can use creativity to develop new products, services, and marketing strategies to stand out from the competition, but to do that you first have to learn by trial and error.

• Don’t be afraid to ask for help, especially if you don’t know something about a particular topic. We all have been there, but if you raise your hand you’ll speed up the process of learning.

• When looking for advice remember that the people that know you the best are the ones who can provide the most valuable insights.

• Know when to baton pass. Recognize when it's time to hand off a task or project to someone else who is better equipped to handle it. You have to understand when it's time to delegate or collaborate with others to achieve a common goal.

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